What Has Been the Greatest Disappointment in Your Life?

Business is putting him in a bad mood
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One of the most common questions asked in job interviews is, "What has been the greatest disappointment in your life?" Your response to this question will help the interviewer determine how easily you are discouraged, how you recover from difficult experiences, and whether you take responsibility for navigating challenging circumstances. Also, interviewers use this type of question to probe for failures in your personal or professional life that might reveal weaknesses which would limit your effectiveness on the job.

Stay Away from Work Disappointments if Possible

Employers may give you some leeway by leaving the context of your disappointment open-ended. In this case, one viable strategy is to avoid referencing a disappointment that happened at work (such as not getting a promotion you wanted). If possible, tell about a more personal disappointment, i.e., the early death of a parent, or an event that changed your academic or career goals.

Believe it or not, it is also okay to not have had a "greatest" disappointment. However, in that case, provide an example of one particularly disappointing experience, or speak more generally about how you would handle a disappointing moment.

Choose Situations Which Can be Viewed as Successes

You can respond directly to this type of question by mentioning a disappointment where you fell short of a very high expectation that you set for yourself. By doing so, you establish that you are a driven employee who strives for a high level of achievement.

For example, you might say: "My first year in sales I set a goal to be the leading salesperson in our office of nine salespeople. I was somewhat naive since most of the other staff were seasoned sellers with extensive product knowledge and well-developed relationships with clients. I was very disappointed when I ended up 4th in sales after my first year. So, I attended some sales seminars and studied hard to learn everything possible about our product. By the end of my third year, I was the leading salesperson in the office."

Connect Your Recovery to Job Requirements

No matter what your answer, be sure to explain how you recovered from (or how you would recover from) your disappointment. Try to emphasize how your ability to recover displays a particular quality that is important for the job. For example, if you say you were unable to afford college right after high school, explain how you worked hard over the next year to save up money. It will demonstrate your perseverance and dedication to your goals.

Examples of Best Answers

  • I set a goal last year to increase our loan volume at the branch to 25 million dollars. I was very disappointed when I came up 2 million short. Our branch still came in 3rd out of 23 branches in the Northeast region, and I have consulted with those branch leaders and picked up some ideas to expand sales next year. 
  • My biggest disappointment is that I wasn’t able to follow my dream of being a professional dancer. I was injured as a teenager during a performance and was never able to move quite as fluidly again. Even though I was disappointed at the time, I realize now that if I had taken that direction, I would not have my advanced degrees and a career I love.
  • My biggest disappointment is that my dad passed away just before I graduated from college and got my first job. He was a pioneer in the technology industry, and he was so proud of me following in his footsteps at such an exciting time in our industry.
  • I set a goal to be on the Dean's List every semester in college and was very disappointed when I missed the mark during the first semester of my junior year. I was working 25 hours a week and took 21 credits that semester. I reduced my work hours to 15 and took 18 credits the next semester and achieved highest honors.
  • Of all the disappointments in my life, the greatest one at the time was when I wasn’t able to go straight to college out of high school. I think the two years I spent working helped me to focus on what I wanted to study and ultimately made my college experience much better. Having a little extra time to figure things out, I was much better prepared to make decisions about what I wanted to study and how that would prepare me for my career.
  • I was very disappointed when I was hired for a top retailer's training program and was placed in the store management track when I had my heart set on the buyer track. As it ends up, my strengths in employee engagement, inventory planning, and sales have enabled me to progress rapidly to my assistant store manager position, and the disappointment was a blessing in disguise.